Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
  • C09B1/52—Amino-hydroxy-anthraquinones; Ethers and esters thereof sulfonated
  • C09B1/523—N-substituted amino and hydroxy anthraquinone
  • C09B1/525—N-aryl derivatives
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
  • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated

Definitions

• This invention relates to acid anthraquinone dyestuffs.
• dyestufis are, 1-amino-(-methylamino-, or -hydroxy-) '4-phenylaminoanthraquinonesulionic acids which are distinguished by carrying a short-chain (C3C7) alkyl substituent in the phenyl radical.
• the presence of the alkly substituent improves the dyestufis. For instance it improves them in respect of the fastness to washing and milling of the shades which they yield when dyed on wool.
• sulfo substituent may be introduced by sulfonating or where there is a halogen substituent in the 3-position if desired by treating with a soluble sulfite.
• the alkylaniline may also carry halogen or methyl substituents.
• Interaction of the anthraquinone derivative with the analine may be efiected for example by heating in a solvent with a copper catalyst and an acid absorber; the solvent may be for instance pyridine or excess of the aniline or where there is a sulfo group present it may be water. Sulfonation may be done with concentrated sulfuric acid or oleum and replacement of the halogen substituent with a sulfonic' acid substituent by heating with a soluble sulfite in a mixture of for example phenol and water; 7
• the following examples illustrate, but do not limit the invention, the parts being by weight.
• Example 1 -19 parts of 1:3-dibromo-4-aminoanthraquinone, 15 parts of -aminobutylbenzene (Hickinbottom, J. Chem. Soc., 1930, 1565), 5 parts of'potassium acetate, 0.4 part of crystalline copper acetate and. parts of pyridine are stirred at 115-120 C., for 16 hours. The mixture is cooled,
• the product is a blue crystalline substance, soluble in benzene with a bright blue colour. It is Z-bromo-I-amino- I-pbutylanilinoanthraquinone.
• the new dyestufi 1-amino-4- butylanilinoanthraquinone-2-sulfonic acid after drying and powdering is a blue solid, readily soluble in water with a bright blue colour. It dyes l5 wool from an acid bath in blue shades which show better washing and milling fastness compared with 1-amino-4-anilinoanthraquinone-2-sulfonic acid.
• Example 2 -16 parts of 4-amino-isoamylben- 20 zene' (prepared by the method described for 4- aminobutylbenzene 10c. cit., but using isoamyl instead of butyl alcohol) are used instead of the 15 parts of 4-aminobutylbenzene and the process otherwise done as in Example 1.
• a dyestufi is 25 obtained which is similar to that of Example 1, but which has even better washing and milling fastness. 1
• the product 2-bromo-1-amino-4-p-n-butyl-otoluidinoanthraquinone, is a blue crystalline substance soluble in benzene with bright blue colour.
• the so-obtained new dyestufi, 1-amino-4-p-nbutyl-o-toluidinoanthraquinone-2-sulfonic acid is a bright blue powder which dissolves in hot water and dyes wool from a neutral or weakly acid bath in bright blue shades having the same washing and milling fastness as those of the dyestuff of Example 1.
• Example 4.10 parts of the condensation product i. e. 2-bromo-1-amino-4-p-isoamylanilinoanthraquinone of Example 2 are dissolved in 100 parts of 100% sulfuric acid, 30 parts of oleum (20% S03) .are added at 20 0., and the dyestuff precipitated in 300 parts of ice water, filtered off, washed with weak brine containing a little sodium carbonate and dried at 100 C.
• the new dyestuff Z-bromo-l-amino--p-isoamylanilinoanthraquinone sulfonic acid dissolves in concentrated sulfuric acid with a blue colour and in boiling water yields bright blue solutions which dye wool from a neutral or weakly acid bath, in blue shades of better-fastness to severe washing and milling than those from the analogous p-toluidino dyestuff.
• the so-obtained compound is treated with sodium sulfite in phenol and water as in Example 1.
• the resulting dyestuif l-aminol-p-heptyl anilinoanthraquinone-2-sulfonic acid dyes wool from a neutral or slightly acid bath in shades which are even faster to severe washing and millmg than those from the dyestuff of Example 1.
• the new product, l-p-isoamylanilino-l-hydroxyanthraquinone is a violet crystalline substance melting at C. It dissolves in concentrated sulfuric acid with a green colour.
• the new dyestuff l-p-isoamylam'lino--hydroxyanthraquinonesulfonic acid is a violet powder which dissolves in water with a violet colour and dyes wool from a neutral or dilute acid bath in violet shades which have better fastness to severe washing and milling than those from the analogous p-toluidino dyestufl.
• Example 7.1 part of the dyestuff from Example 1 is dissolved in 3000 parts of water containing 1.5 parts of sodium cetyl sulfate 15% paste. 50 parts of well-wetted woolen yarn are entered, the dye-bath raised to the boil in hour and maintained at the boil for 1 hour. The dyed yarn is removed, rinsed in cold water and dried. The wool is dyed in blue shades which are brighter than when no sodium cetyl sulfate is used.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Coloring (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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ID=10320569

Family Applications (1)

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• 1934
  • 1934-10-31 GB GB31268/34A patent/GB446819A/en not_active Expired
  • 1934-11-14 GB GB32827/34A patent/GB449011A/en not_active Expired
• 1935
  • 1935-10-28 US US47201A patent/US2049648A/en not_active Expired - Lifetime
  • 1935-10-30 DE DEI53521D patent/DE642726C/de not_active Expired
  • 1935-10-31 FR FR797119D patent/FR797119A/fr not_active Expired
  • 1935-11-14 FR FR46717D patent/FR46717E/fr not_active Expired

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